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P8761

Sigma-Aldrich

Probenecid

≥98% (NaOH, titration), powder, uricosuric agent

Synonym(s):

p-(Dipropylsulfamoyl)benzoic acid

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About This Item

Empirical Formula (Hill Notation):
C13H19NO4S
CAS Number:
57-66-9
Molecular Weight:
285.36
EC Number:
200-344-3
MDL number:
MFCD00038402
UNSPSC Code:
12161501
PubChem Substance ID:
24898976
NACRES:
NA.77

product name

Probenecid,

Assay

≥98% (NaOH, titration)

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

SMILES string

CCCN(CCC)S(=O)(=O)c1ccc(cc1)C(O)=O

InChI

1S/C13H19NO4S/c1-3-9-14(10-4-2)19(17,18)12-7-5-11(6-8-12)13(15)16/h5-8H,3-4,9-10H2,1-2H3,(H,15,16)

InChI key

DBABZHXKTCFAPX-UHFFFAOYSA-N

Gene Information

human ... SLC22A11(55867) , SLC22A6(9356) , SLC22A8(9376)

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Application

Probenecid has been used:
  • as a component of phenol red free Hank′s buffer for Intracellular Ca2+-mobilization assay
  • as a component of calcium sensitive dye for calcium mobilization Studies
  • as a supplement in Hank′s balanced salt solution (HBSS) assay buffer

Useful as an inhibitor of the organic anion transporter, MRP.

Biochem/physiol Actions

Probenecid is a uricosuric agent, which increases uric acid removal in the urine and reduces urate reuptake. It also reduces the renal tubular excretion of many other drugs and increases their plasma concentration. The inhibitory action of probenecid is mediated by organic anion transporters. It is found useful for the treatment of gout. Probenecid is responsible for the rise in the levels of neurochemicals in the brain by preventing its movement from choroid plexus and parenchyma cells into plasma.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Probenecid, a gout remedy, inhibits pannexin 1 channels
Harris D, et al.
American Journal of Physiology. Cell Physiology, 295, C761?C767-C761?C767 (2008)
The
Drugs of Abuse: Neurological Reviews and Protocols, 109-109 (2003)
Determining the potency and molecular mechanism of action of insurmountable antagonists.
Kenakin, T, et al.
Journal of Pharmacology and Experimental Therapeutics, 319, 710-723 (2014)
Lipid phosphate phosphatase-1 expression in cancer cells attenuates tumor growth and metastasis in mice
Tang X, et al.
Journal of Lipid Research, 55, 2389-2400 (2014)
Hiroshi Watanabe et al.
Kidney international, 83(4), 582-592 (2013-01-18)
The accumulation of p-cresyl sulfate (PCS), a uremic toxin, is associated with the mortality rate of chronic kidney disease patients; however, the biological functions and the mechanism of its action remain largely unknown. Here we determine whether PCS enhances the
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